#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:20:24 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301776 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/98/1519856.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1519856
loop_
_publ_author_name
'Besli, S.'
'Kilic, A.'
'Davies, David B.'
'Coles, Simon J.'
'Coles, Simon J.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C18H24N5O2P3S2
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              286
_journal_year                    2007
_chemical_formula_sum            'C18 H24 N5 O2 P3 S2'
_chemical_formula_weight         499.45
_space_group_IT_number           78
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.50090(10)
_cell_length_b                   11.50090(10)
_cell_length_c                   16.78340(10)
_cell_measurement_reflns_used    93378
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2219.95(3)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            56772
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.7605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4987
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0218
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0265P)²+0.6723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0533
_refine_ls_wR_factor_ref         0.0539
_reflns_number_gt                4844
_reflns_number_total             4987
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-286.cif
_cod_data_source_block           2007src0258
_cod_depositor_comments
;
Citation :
Besli, S and Kilic, A. and Davies, David B. and Coles, Simon J. and 
Coles, Simon J. and Hursthouse, Michael B. (2007) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/286)

More at:
http://ecrystals.chem.soton.ac.uk/286/
;
_cod_original_sg_symbol_H-M      P43
_cod_database_code               1519856
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.33720(15) 0.20863(14) -0.13795(10) 0.0200(3) Uani 1 1 d . . .
C2 C 0.45675(15) 0.20822(16) -0.15123(11) 0.0255(4) Uani 1 1 d . . .
H2 H 0.4931 0.1416 -0.1736 0.031 Uiso 1 1 calc R . .
C3 C 0.52272(17) 0.30517(18) -0.13175(12) 0.0313(4) Uani 1 1 d . . .
H3 H 0.6043 0.3050 -0.1406 0.038 Uiso 1 1 calc R . .
C4 C 0.46944(19) 0.40213(17) -0.09934(12) 0.0332(4) Uani 1 1 d . . .
H4 H 0.5147 0.4684 -0.0858 0.040 Uiso 1 1 calc R . .
C5 C 0.35026(19) 0.40305(16) -0.08655(12) 0.0328(4) Uani 1 1 d . . .
H5 H 0.3142 0.4700 -0.0644 0.039 Uiso 1 1 calc R . .
C6 C 0.28317(17) 0.30636(16) -0.10598(11) 0.0267(4) Uani 1 1 d . . .
H6 H 0.2015 0.3071 -0.0975 0.032 Uiso 1 1 calc R . .
C7 C 0.33088(14) -0.20922(14) -0.12030(10) 0.0175(3) Uani 1 1 d . . .
C8 C 0.34999(16) -0.20840(16) -0.20191(11) 0.0255(4) Uani 1 1 d . . .
H8 H 0.2914 -0.1804 -0.2369 0.031 Uiso 1 1 calc R . .
C9 C 0.45492(18) -0.24859(17) -0.23251(12) 0.0321(4) Uani 1 1 d . . .
H9 H 0.4684 -0.2478 -0.2884 0.039 Uiso 1 1 calc R . .
C10 C 0.53941(17) -0.28965(17) -0.18112(15) 0.0367(5) Uani 1 1 d . . .
H10 H 0.6110 -0.3176 -0.2019 0.044 Uiso 1 1 calc R . .
C11 C 0.52069(17) -0.29044(17) -0.09984(14) 0.0349(5) Uani 1 1 d . . .
H11 H 0.5798 -0.3180 -0.0651 0.042 Uiso 1 1 calc R . .
C12 C 0.41585(16) -0.25114(15) -0.06853(11) 0.0243(4) Uani 1 1 d . . .
H12 H 0.4024 -0.2528 -0.0127 0.029 Uiso 1 1 calc R . .
C13 C 0.60893(14) 0.12316(15) 0.02968(10) 0.0212(3) Uani 1 1 d . . .
H13A H 0.6692 0.1829 0.0198 0.025 Uiso 1 1 calc R . .
H13B H 0.5939 0.0815 -0.0209 0.025 Uiso 1 1 calc R . .
C14 C 0.65109(14) 0.03802(15) 0.09275(11) 0.0231(3) Uani 1 1 d . . .
H14A H 0.7229 -0.0004 0.0736 0.028 Uiso 1 1 calc R . .
H14B H 0.6705 0.0814 0.1419 0.028 Uiso 1 1 calc R . .
C15 C 0.56108(15) -0.05399(15) 0.11209(11) 0.0236(4) Uani 1 1 d . . .
H15A H 0.5473 -0.1030 0.0645 0.028 Uiso 1 1 calc R . .
H15B H 0.5906 -0.1047 0.1553 0.028 Uiso 1 1 calc R . .
C16 C -0.05487(14) 0.10229(15) 0.14191(10) 0.0211(3) Uani 1 1 d . . .
H16A H -0.0978 0.0716 0.1885 0.025 Uiso 1 1 calc R . .
H16B H -0.0795 0.0580 0.0942 0.025 Uiso 1 1 calc R . .
C17 C -0.08260(14) 0.23064(15) 0.13067(10) 0.0205(3) Uani 1 1 d . . .
H17A H -0.1670 0.2399 0.1211 0.025 Uiso 1 1 calc R . .
H17B H -0.0628 0.2734 0.1800 0.025 Uiso 1 1 calc R . .
C18 C -0.01568(14) 0.28288(14) 0.06114(10) 0.0200(3) Uani 1 1 d . . .
H18A H -0.0414 0.2461 0.0108 0.024 Uiso 1 1 calc R . .
H18B H -0.0322 0.3672 0.0577 0.024 Uiso 1 1 calc R . .
N1 N 0.36889(11) 0.01090(11) -0.00542(8) 0.0163(3) Uani 1 1 d . . .
N2 N 0.28645(12) 0.14655(12) 0.11531(8) 0.0178(3) Uani 1 1 d . . .
N3 N 0.13947(11) 0.06592(12) 0.00083(8) 0.0184(3) Uani 1 1 d . . .
N4 N 0.49990(12) 0.17968(12) 0.05832(8) 0.0173(3) Uani 1 1 d . . .
N5 N 0.07161(12) 0.08802(13) 0.15439(8) 0.0175(3) Uani 1 1 d . . .
O1 O 0.45222(10) -0.00054(10) 0.13695(7) 0.0195(2) Uani 1 1 d . . .
O2 O 0.10964(9) 0.26481(9) 0.07147(7) 0.0177(2) Uani 1 1 d . . .
P1 P 0.24553(3) 0.01056(3) -0.04708(2) 0.01458(8) Uani 1 1 d . . .
P2 P 0.39341(3) 0.08456(3) 0.07381(2) 0.01391(8) Uani 1 1 d . . .
P3 P 0.15696(3) 0.13630(3) 0.08322(2) 0.01424(8) Uani 1 1 d . . .
S1 S 0.25498(4) 0.08168(4) -0.16190(2) 0.02323(9) Uani 1 1 d . . .
S2 S 0.19603(3) -0.15868(3) -0.08061(2) 0.01872(8) Uani 1 1 d . . .
H4N H 0.4806(19) 0.2343(19) 0.0284(13) 0.025(5) Uiso 1 1 d . . .
H5N H 0.090(2) 0.030(2) 0.1720(14) 0.031(6) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 120.33(17) . .
C6 C1 S1 120.72(14) . .
C2 C1 S1 118.95(13) . .
C3 C2 C1 119.95(17) . .
C4 C3 C2 119.87(18) . .
C3 C4 C5 120.30(19) . .
C4 C5 C6 120.34(18) . .
C1 C6 C5 119.21(18) . .
C8 C7 C12 120.45(17) . .
C8 C7 S2 120.26(14) . .
C12 C7 S2 119.28(13) . .
C7 C8 C9 120.00(18) . .
C10 C9 C8 119.54(19) . .
C11 C10 C9 120.59(19) . .
C10 C11 C12 120.42(19) . .
C11 C12 C7 118.99(18) . .
N4 C13 C14 108.91(13) . .
C15 C14 C13 112.38(13) . .
O1 C15 C14 110.73(13) . .
N5 C16 C17 109.35(13) . .
C18 C17 C16 111.85(14) . .
O2 C18 C17 110.52(13) . .
P1 N1 P2 121.75(8) . .
P2 N2 P3 123.10(9) . .
P1 N3 P3 122.47(8) . .
C13 N4 P2 112.51(11) . .
C16 N5 P3 116.57(11) . .
C15 O1 P2 115.72(10) . .
C18 O2 P3 118.92(10) . .
N1 P1 N3 117.55(7) . .
N1 P1 S1 111.03(5) . .
N3 P1 S1 110.35(6) . .
N1 P1 S2 111.29(5) . .
N3 P1 S2 107.30(6) . .
S1 P1 S2 97.42(2) . .
N2 P2 O1 108.29(7) . .
N2 P2 N1 117.81(7) . .
O1 P2 N1 107.58(7) . .
N2 P2 N4 110.17(7) . .
O1 P2 N4 101.27(7) . .
N1 P2 N4 110.36(7) . .
O2 P3 N2 107.13(7) . .
O2 P3 N3 108.52(7) . .
N2 P3 N3 116.39(7) . .
O2 P3 N5 101.55(7) . .
N2 P3 N5 109.81(7) . .
N3 P3 N5 112.26(7) . .
C1 S1 P1 98.02(6) . .
C7 S2 P1 99.55(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.392(2) .
C1 C2 1.393(2) .
C1 S1 1.7853(17) .
C2 C3 1.388(3) .
C3 C4 1.384(3) .
C4 C5 1.387(3) .
C5 C6 1.392(3) .
C7 C8 1.387(2) .
C7 C12 1.394(2) .
C7 S2 1.7851(16) .
C8 C9 1.391(3) .
C9 C10 1.382(3) .
C10 C11 1.381(3) .
C11 C12 1.391(3) .
C13 N4 1.492(2) .
C13 C14 1.521(2) .
C14 C15 1.516(2) .
C15 O1 1.456(2) .
C16 N5 1.479(2) .
C16 C17 1.522(2) .
C17 C18 1.522(2) .
C18 O2 1.4665(19) .
N1 P1 1.5817(13) .
N1 P2 1.6018(13) .
N2 P2 1.5832(14) .
N2 P3 1.5880(13) .
N3 P1 1.5937(14) .
N3 P3 1.6148(14) .
N4 P2 1.6626(14) .
N5 P3 1.6427(14) .
O1 P2 1.5933(11) .
O2 P3 1.5874(11) .
P1 S1 2.0963(6) .
P1 S2 2.1046(6) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045287
